Anthracene dye and process of making same.



UNITED sTA'rEs PATENT OFFICE.

OSCAR RALLY, or MANNHEIM, GERMANY, AssIGNoa 'ro' BADISCHE ANILIN- & sonArABRIK, or LUDWIGSHAFEN-ON-THE-RHINE, GERMANY, A CORPORATION.

ANTHRACENE DYE AND PROCESS OF MAKING SAME.

1,037,410. No Drawing.

Specification oi. I Letters Patent.

Application filed September 20, 1910. Serial No. 582,917.

Patented Sept. 3, 1912.

vented new and useful- Improvements in' Anthracene Dye and Processes ofMaking ,Same, of which the following is a specification.

This invention relates to the production -of coloring matters of theanthracene series.

I have discovered that halogenated diphenylmethane compounds of aconstitution corresponding to the general formula (in which Itrepresents a benzene nucleus, either substituted or not, and Xrepresents a neutral substituent containing hydrogen, under which term Iinclude either-hydrogen, or alkyl or aryl, or aralkyl) can be condensedwith aminoanthraquinone bodies and that the products of suchcondensation contain at least one anthraquinone residue attached to adiphenyl-methane residue by means of an amino group, and can be employedin the unsulfonated form as vat coloring matters, or in the sulfonatedform they can be used for dyeing wool.

The following is an example of how 111 invention can be carried intopractical e feet, but the invention is not confined to this example. Theparts fare by weight. Boil together, in a reflux apparatus, fifty partsof 4.4='-dichlor-diphenyl-methane, one hundred parts of 1 aminoanthraquinone, twenty parts of calcined soda, two parts of copper oxidand fifteen hundred parts of nitrobenzenet When the reaction isfinished,

allow the mass to cool, filter oflf the reaction product, wash the masswith alcohol, and dry it. It is then a reddish brown powder which isfairly easily soluble in hot ni'trobenzene the solution bein red, and itis soluble in concentrated .sul uric acid, the solution being of anolive color, and it is also soluble in fuming sulfuric acid oftwentythree per cent. free SO the solution being green. It dyes, cottonfrom the vat, yielding Bordeaux-red shades of great fastness. Ontreating it with fuming sulfuric acid at 30 C., until a test portiongives a clear solution which dyes wool brilliant red shades. The

in water, it is converted into a sulfonic acid product possesses aconstitution corresponding to the formula CO NH (\i/CHS\(\ NH CO NvC- MALil, Ude

In a similar manner, other halogenated diphe'nyl-methane compounds canbe employed, and, instead of l-amino-anthraquinone, other aminocompounds of anthraquinone, or derivatives thereof, can be used. In-

stead of copper oxid, other suitable condensation agent, such forinstance as cuprous chlorid, can be used.

Now what I claim is l. The process of producing coloring matters of theanthracene series by treating a halogenated diphenyl-methane compound ofa constitution corresponding to the formula HlR-CX:RHL

where R represents a benzene nucleus and X represents a neutralsubstituent' containing hydrogen, with an amino compound of theanthraquinone series.

, 2. The process for producing coloring' matter of the anthracene seriesby condensing 4.4-dichlor-diphenyl-methane with 1- amino-anthraquinone.

3. As new articles of manufacture the coloring matters of the anthraceneseries which probably possess a constitution corresponding to theformula where A is an anthraquinone nucleus,R is a benzene nucleus and Xis a neutral substituent containing hydrogen, which colorlng matters canbe employed in the unsulfonated form as vat coloring matters and in thesulfonated form can be used for dyeing wool.

' 4. As a newarticle of manufacture the coloring matter which probablypossesses a constitution corresponding to the formula which coloringmatter consists when dry of a reddish brown powder which ylelds a redsolution in hot nitrobenzene; an olive solu- ,Iniestimony whereof'i havehereunfoset tion in concentrated sulfuric acid, and a my hand-in thepresence of two subscrlbmg green solution in fuming sulfuric acid ofwltnesses.

twenty-three per cent. free S0 and-which OSCAR BALLY. 5 whenunsulfonated dyes cotton from-the vat Witnesses:

Bordeaux red, while inthe sulfonat'ed form T. ALEc. LLOYD,

if) dyes wool bl illiant i'ed shades. J OSEF 'Pmmn.

